Bay-Substitution of Perylene Bisimides with Bidentate Nucleophiles: The Case of Aryloxide Anions
Date
2024-01-25Author
Rivas, Carlos J.
Mena, Leandro D.
Baumgartner, María T.
Jimenez, Liliana B.
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In this study, we delve into the regioselectivity of nucleophilic reactions involving brominated perylene bisimides (PBIs) and various bidentate aryloxide anions, previously associated with an SRN1 mechanism. We present herein a new perspective, suggesting that a single-electron-transfer aromatic nucleophilic substitution (SeT-SNAr) mechanism is a more plausible scenario. Our study reveals the favorable impact of photostimulation on reaction yields, making our method a convenient approach for accessing O-arylated PBIs.
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Rivas, C. J., Mena, L. D., Baumgartner, M. T., & Jimenez, L. B. (2024). Bay-Substitution of Perylene Bisimides with Bidentate Nucleophiles: The Case of Aryloxide Anions. The Journal of Organic Chemistry, 89(4), 2764-2770.
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https://pubs.acs.org/doi/abs/10.1021/acs.joc.3c02002https://www.sciencedirect.com/org/science/article/abs/pii/S0022326324001257
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